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Headway

Senior Engineering Manager, Web Platform

Headway

. Lead a small, senior team of five frontend engineers .

Posted 10/15/2026full-timeRemote • United StatesSenior💰 $265,200 - $331,500 per yearWebsite

Tech Stack

Tools & technologies
ReactTypeScript

About the role

Key responsibilities & impact
  • Lead a small, senior team of five frontend engineers
  • Own the vision and strategy for how Headway builds UI
  • Set strategy for the Helix design system and web architecture
  • Serve as the voice of frontend engineering across the company
  • Set the roadmap with Design and Engineering Foundations leadership
  • Demonstrate the value of platform work through clear metrics
  • Stay close to the code by opening pull requests, reading and changing code with AI tools, and taking on small pieces of work
  • Hire to a high bar, develop team members, and address underperformance
  • Give senior engineers ownership of technical direction
  • Explain frontend strategy to engineers, designers, and executives
  • Evolve Helix with Design leadership
  • Own frameworks, tooling, and standards for accessibility, performance, testing, and maintainability across Headway web applications
  • Provide AI agents with skills, documentation, and guardrails for frontend development
  • Build automated checks and agent reviews for frontend code
  • Grow Headway’s frontend guild
  • Gather product engineering feedback and incorporate it into the roadmap
  • Prioritize planned work, support requests, and new initiatives
  • Advocate for appropriate frontend team headcount
  • Participate in recruiting screens, leadership interviews, product sense interviews, and frontend technical interviews

Requirements

What you’ll need
  • Senior or staff frontend engineering background before moving into management
  • Deep experience with React and the modern web
  • Experience leading a frontend platform, design system, or web architecture team
  • 3+ years managing engineers
  • Experience hiring, developing senior engineers, and managing performance, including addressing underperformance
  • Recent experience shipping code with AI tools within the last six months
  • Clear point of view on modern frontend engineering and ability to advocate with data
  • Ability to explain platform work value to product teams and executives
  • Experience partnering closely with Design and translating design system decisions into engineering plans
  • Experience building alignment across several product teams with competing priorities
  • Comfortable working at a fast pace with plans measured in weeks or a few months
  • Knowledge of TypeScript, React, React Router 7, Vite, Tailwind CSS, Helix, Datadog, PagerDuty, Sentry, GitHub, Cursor, Claude, Gemini, and Eddy
  • Knowledge of accessibility standards including WCAG 2.1 AA
  • Authorization to work in the United States for any employer

Benefits

Comp & perks
  • Robust health and wellness benefits
  • Retirement savings
  • Meaningful ownership opportunities through equity
  • Reasonable accommodations for persons with disabilities
  • Employee equity details provided with the offer